US4134850A - Bleaching composition - Google Patents
Bleaching composition Download PDFInfo
- Publication number
- US4134850A US4134850A US05/683,811 US68381176A US4134850A US 4134850 A US4134850 A US 4134850A US 68381176 A US68381176 A US 68381176A US 4134850 A US4134850 A US 4134850A
- Authority
- US
- United States
- Prior art keywords
- peroxyacid
- group
- bleaching agent
- bleaching
- aliphatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 238000004061 bleaching Methods 0.000 title claims abstract description 26
- 150000004965 peroxy acids Chemical class 0.000 claims abstract description 39
- 239000003599 detergent Substances 0.000 claims abstract description 20
- 239000003085 diluting agent Substances 0.000 claims abstract description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims abstract description 7
- 235000019341 magnesium sulphate Nutrition 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 230000001066 destructive effect Effects 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- -1 aliphatic peroxyacid Chemical class 0.000 claims description 47
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 16
- 239000007844 bleaching agent Substances 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 235000011152 sodium sulphate Nutrition 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 239000003082 abrasive agent Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 238000005282 brightening Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012933 diacyl peroxide Substances 0.000 abstract description 12
- 238000005406 washing Methods 0.000 abstract description 9
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 239000005639 Lauric acid Substances 0.000 abstract 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 description 19
- 239000002243 precursor Substances 0.000 description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001263 acyl chlorides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000006057 Non-nutritive feed additive Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- MUTGBJKUEZFXGO-WDSKDSINSA-N (3as,7as)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@H]21 MUTGBJKUEZFXGO-WDSKDSINSA-N 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960001922 sodium perborate Drugs 0.000 description 2
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- FPCPOLLWTJARLO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)acetic acid Chemical compound CC(=C)C(=O)OCC(O)=O FPCPOLLWTJARLO-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 description 1
- FKHZOILQVUFMTD-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dicarboxylic acid Chemical compound OC(=O)C1C=CC(C(O)=O)C=C1 FKHZOILQVUFMTD-UHFFFAOYSA-N 0.000 description 1
- PKMGFABZWDMZHC-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboperoxoate Chemical compound C1CCCCC1C(=O)OOC(=O)C1CCCCC1 PKMGFABZWDMZHC-UHFFFAOYSA-N 0.000 description 1
- TZXIQUKODWCMNA-UHFFFAOYSA-N cyclohexene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C=C(C(O)=O)C1 TZXIQUKODWCMNA-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002081 peroxide group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- NVVOIJGOEFSXRM-UHFFFAOYSA-N tert-butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)(C)C NVVOIJGOEFSXRM-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
- C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3945—Organic per-compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to bleaching compositions and to processes for bleaching.
- a bleaching composition or detergent composition containing (a) an aliphatic peroxyacid having general formula: ##STR3## WHEREIN M AND N EACH REPRESENT AN INTEGER OF FROM 0 TO 5, PROVIDED N + M ⁇ 1 OR MONO- OR DIETHYLENICALLY UNSATURATED DERIVATIVES THEREOF, OR AN ANION THEREOF, OR (B) A PRECURSOR OF THE ALIPHATIC PEROXYACID, AND IF NECESSARY A DONOR OF PERHYDROXYL ANIONS.
- the peroxyacid or precursor thereof can be substituted by a lower alkyl, chloro or nitro group.
- a composition suitable for mixing with a surfactant and optionally other conventional components to form a heavy duty washing composition (a) an aliphatic peroxyacid having general formula: ##STR4## WHEREIN M AND N EACH REPRESENT AN INTEGER OF FROM 0 TO 5, PROVIDED N + M ⁇ 1 OR MONO- OR DIETHYLENICALLY UNSATURATED DERIVATIVES THEREOF, OR AN ANION THEREOF, OR (B) A PRECURSOR OF THE ALIPHATIC PEROXYACID, AND IF NECESSARY A DONOR OF PERHYDROXYL ANIONS, MIXED WITH A DETERGENT BUILDER AND/OR A PROCESSING ADDITIVE AND OPTIONALLY COMPONENTS OF HEAVY DUTY WASHING COMPOSITIONS OTHER THAN THE SURFACTANT.
- the peroxyacid can be generated in solution by hydrolysis or perhydrolysis of the precursor.
- One class of favoured precursors comprises acyl peroxides, from which peracids can be generated by both hydrolysis and perhydrolysis.
- n + n can vary between 1 and 5.
- dicarboxylic acids contain at least one assymetric carbon atom so that the peroxyacids can be cis or trans, and in some cases contain optically active forms. Many preparations result in mixtures.
- m + n is 2, for example peroxy derivatives of cyclohexane-1,2,3-, -1,2,4- or -1,3,5-tricarboxylic acids, and corresponding ethylenically unsaturated compounds such as 1-cyclohexene-1,3,5-tricarboxylic acid.
- n 4 or 5 or n is 5, i.e. peroxy derivatives of cyclohexane-1,2,3,4,5,6-hexacarboxylic acid.
- some of the peroxycompounds contain at least one moiety containing two or more carboxy or peroxycarboxy groups in 1, 3 or 1,4 positions.
- production of diacyl peroxides can lead to formation of polymeric acyl peroxides, i.e. compounds containing at least two acyl peroxide linkages, especially if the moiety intentionally contains more than one peroxide group. Since such polymeric acyl peroxides also form the requisite peroxyacids in aqueous solution, they are included within the present invention. It will also be recognised that others of the peroxy compounds contain two vicinal peroxycarboxy groups.
- the alicyclic peroxyacids preferably contain more than one peroxyacid group, and advantageiously do not contain carboxy groups, because, in general, such a preferred arrangement allows a given amount of active oxygen to be provided in a smaller amount of alicyclic compound, and secondly absence of carboxy groups seems to result in more efficient use of the active oxygen for bleaching.
- favoured precursors of the peroxyacids are the corresponding acyl peroxides.
- diacyl peroxides e.g. 2,2'-dicarboxy cyclohexanoyl peroxide, or internal acyl peroxides, e.g. bicyclo(4,4,0)-2,3-dioxadecane-1,4-dione, can be formed.
- diacyl peroxides include 3,3'-dicarboxy-, 3,3'-diperoxycarboxy-, 4,4'-dicarboxy-, and 4,4'-diperoxycarboxydicyclohexanoyl peroxide, 2,2'-dicarboxy and 2,2'-diperoxycarboxydicyclohex-1-enoyl peroxide, 2,2'-dicarboxy-, and 2,2'-diperoxycarboxydicyclohex-4-enoyl peroxide and 4,4'-dicarboxy and 4-4'-diperoxycarboxydicyclohex-2-5-dienoyl peroxide, when n is 1.
- suitable peroxides include 2,2',3,3'-tetracarboxy-, 2,2',3,3'-tetraperoxycarboxy-, 2,2',4,4'-tetracarboxy-, and 2,2',4,4'-tetraperoxycarboxy-, 3,3',5,5'-tetracarboxy-, and 3,3',5,5'-tetraperoxycarboxydicyclohexanoyl peroxide and 3,3',5,5'-tetracarboxy-, and 3,3',5,5'-tetraperoxycarboxydicyclohex-1-enoyl peroxide.
- suitable peroxides include 2,2',3,3',4,4'-hexacarboxydicyclohexanoyl peroxide and when n is 5, 2,2',3,3',4,4',5,5',6,6'-decacarboxydicyclohexanoyl peroxide.
- asymmetric peroxides based on the moieties employed in the symmetric peroxides aforementioned, can be used.
- the other moiety completing the diacyl peroxide can be one of the remaining moieties aforementioned, or any other compatible acyl group.
- Compatible groups can be aromatic such as phthaloyl, isophthaloyl, terephthaloyl, trimesoyl or pyromellitoyl or the corresponding groups in which the carboxy group or groups is n are replaced by a peroxycarboxy group or groups, the aromatic groups optionally being substituted by lower alkyl, chloro or nitro groups.
- the aromatic group can also be benzoyl, optionally substituted by lower alkyl, chloro or nitro groups.
- Compatible groups can also be aliphatic, such as acetyl, succinyl and glutaryl.
- compositions having a median point of at least 200 kg-cm are considered to be non-hazardous in the test, but to provide a greater margin of safety compositions preferably have a median point of at least 300 Kg-cm.
- the desensitising amount is selected within the range of 1 to 10 parts by weight of diluent per part of bleaching agent.
- the desensitising diluent can be selected from hydrocarbons having melting points in excess of 30° C., e.g. microcrystalline waxes, aliphatic fatty acids, e.g. lauric and stearic acids, aromatic acids e.g. benzoic acid, alkyl esters of the aliphatic or aromatic acids, e.g.
- t-butyl stearate protein or starch materials, boric acid, aluminium sulphate, clays, aluminosilicates, and especially alkali and alkaline earth metal salts of halogen-free acids having a first dissociation constant of at least 1 ⁇ 10 -3 , e.g. sodium sulphate, magnesium sulphate and sodium tripolyphosphate.
- sodium sulphate is an example of a processing aid and sodium tripolyphosphate is an example of a detergent builder.
- the intimate contact can be by way of admixing particles of the diluent with the alicyclic peroxyacid or peroxide or by granulating or coating the alicyclic peroxyacid or peroxide with the diluent. More than one diluent may be employed, conveniently first contacting the alicyclic peroxyacid or peroxide with an unreactive diluent described hereinbefore, and then coating the mixture with a second diluent.
- Such second diluent can be selected from fatty acid alkanolamides, fatty alcohol polyglycol ethers, polyglycol and polypropylene oxide polymers, alkaryl polyglycol ethers, polyethylene glycol and fatty acid esters and, amides thereof, and esters and amides of glycerol and sorbitol, polyvinyl alcohol, polymethyl methacrylate, dextrin, starch, gelatin carboxymethyl methacrylate, solid hydrocarbons, aliphatic fatty acids, fatty alcohols, sodium sulphate and magnesium sulphate.
- “Fatty” in the terms “fatty alcohol” and “fatty acid” is used to denote at least 12, desirably from 12 to 26 carbon atoms in the longest chain. Normally the amount of coating is within the range of 3% to 35% by weight based on the weight of the coated product. Alicyclic peroxyacid or peroxide thus coated is less prone to decomposition when stored in contact with alkaline surfactants, such as sodium salts or alkyl benzene sulphonates, which are commonly employed in detergent and bleaching compositions.
- alkaline surfactants such as sodium salts or alkyl benzene sulphonates
- peroxyacid precursors other than aycl peroxides are employed, they can be treated in the same way as acyl peroxides if they contain active oxygen they preferably are isolated from other components of the composition by the water soluble or dispersible coating described hereinbefore.
- perhydroxyl anions As referred to hereinbefore certain precursors require perhydroxyl anions to generate peroxyacids.
- the perhydroxyl anions can be provided by separate addition of hydrogen peroxide or any inorganic active oxygen containing compounds hereinafter called persalts such as sodium perborate or sodium percarbonate (the hydrogen peroxide addition product).
- persalts such as sodium perborate or sodium percarbonate (the hydrogen peroxide addition product).
- the bleaching composition of the detergent composition or the composition for mixing with a surfactant contains the persalt in addition to the precursor, advantageously in a mole ratio of from 5:1 to 1:5, particularly in a mole ratio of approximately 1:1, of persalt to precursor, on the assumption that the precursor contains one perhydrolysable site per molecule.
- Each acyl peroxide linkage forms a polymerisable site.
- each precursor molecule contains more than one such perhydrolysable site then the ratio of persalt to precursor is preferably increased "pro rata".
- a diacyl peroxide contains one such site, but a polymeric acyl peroxide contains a plurality of such sites.
- bleaching solutions according to the present invention contain at least 1 ppm available oxygen "av ox" and for use in washing textile fabrics, e.g. cotton or cotton/polyesters often from 5 to 200 ppm "av ox". Solutions for cleaning surfaces such as metal, plastic or wooden surfaces often contain from 200 ppm to 500 ppm "av ox”. If desired, solutions produced by the dissolution of compositions described herein can be used to bleach textile fabrics, wood or pulp under the conditions, and employing the equipment used for bleaching such articles with hydrogen peroxide or inorganic peroxoacids.
- bleaching/washing in the home can take place at ambient temperature or higher, conveniently in the range of 25° to 60° C.
- the bleaching and detergent compositions are each formulated to produce solutions having a pH of between 8.5 and 11.5; preferably from 8.5 to 9.5.
- bleaching or detergent compositions according to the present invention can contain components other than the diacyl peroxide and the inorganic percompound.
- components are selected from detergent builders, diluent salts, surfactants and minor proportions of colours, perfumes, bleach stabilisers, optical brighteners, soil antiredeposition agents, enzyme, dedusting agents, tarnish inhibitors and abrasives.
- Suitable builder salts can be either organic, for example aminopolycarboxylates, organic polyphosphates, sodium citrate or sodium gluconate, or inorganic, for example, alkali metal carbonates, silicates, phosphates, polyphosphates or aluminosilicates.
- builders are present in proportions of from 1% to 90% by weight. Such compounds alter the pH of detergent/bleaching solutions.
- sufficient builder salt is used to adjust the pH of the solution to from pH 7 to 11, more preferably from pH 8 to 11.
- a typical processing aid is sodium sulphate which is conveniently incorporated in detergent/bleaching compositions in an amount of from 1 to 40% by weight.
- builder salt or processing aid has been used to desensitise the diacyl peroxide the amount so used to included in the total amount of builder salt or processing aid present in the composition.
- the surfactants may conventionally be water-soluble anionic, non-ionic, ampholytic or zwitterionic suface active agents. Suitable surfactants are often selected from fatty acids and their alkali metal salts, alkyl sulphonates, especially linear alkyl benzene sulphonates, sulphated aliphatic olefins, sulphated condensation products of aliphatic amides and quaternary ammonium compounds.
- the surfactants are normally present in the detergent composition in amounts of from 1% to 90% by weight, often in a weight ratio to the builder salts of from 2:1 to 1:10. It is believed that in aqueous alkaline media organic peroxyacids are formed from the diacyl peroixde.
- the bleaching composition can include any compound or compounds which enhance the bleaching or washing activity of organic peroxyacids, such as ketones and aldehydes as described in U.S. Pat. No. 3,822,114 or certain quaternary ammonium salts as described in British Pat. No. 1,378,671, both patents to Proctor & Gamble.
- organic peroxyacids such as ketones and aldehydes as described in U.S. Pat. No. 3,822,114 or certain quaternary ammonium salts as described in British Pat. No. 1,378,671, both patents to Proctor & Gamble.
- One convenient method of providing a diluent/peroxyacid or precursor suitable for incorporation in a detergent composition and substantially isolated from alkaline surfactants is to form a mixture of particulate peroxyacid or precursor with a particulate inorganic diluent such as sodium sulphate or tripolyphosphate or magnesium sulphate into tablets or extrudates.
- a particulate inorganic diluent such as sodium sulphate or tripolyphosphate or magnesium sulphate
- Such tablets or extrudates by themselves effectively reduce the surface of the precursor or peroxyacid presented to the alkaline surfactants, and thus alleviate the problem of loss of active oxygen during storage.
- the problem can be further alleviated by providing an outer layer around the tablets or extrudates comprising at least one of the coating compounds described hereinbefore, generally in an amount of up to 20% by weight.
- any suitable organic compounds described hereinbefore may be formed into a flexible sachet within which a diluent/peroxyacid or precursor mixture can be placed.
- the tablet or extrudate, or sachet can also contain the persalt if generation of perhydroxyl anions is required in a mole ratio to the precursor of from 2:1 to 1:2, and preferably approximately 1:1, assuming one perhydrolysable site per precursor molecule.
- the aliphatic peroxyacids described herein can in general be prepared by appropriate oxidation of the corresponding acyl chloride or anhydride.
- gentle oxidation of an anhydride with hydrogen peroxide in ether produces a carboxy group ortho to a peroxycarboxy group, at reflux temperature.
- By carrying out the reaction between the acyl chloride and hydrogen peroxide in non aqueous systems such as methane sulphonic acid substantially all the acyl chloride group present in the molecule can be oxidised to peroxycarboxy groups.
- 2-peroxycarboxycyclohexanecarboxylic acid can be formed by reacting cis or trans cyclohexane-1,2-dicarboxylic anhydride with excess hydrogen peroxide in ether solution at reflux temperature for about 1.5 hours. The aqueous layer is washed with ether to extract organic compounds. The ether fractions are combined, washed with saturated ammonium sulphate solution, dried with magnesium sulphate and evaporated to dryness leaving a white solid which is the product.
- Acyl peroxides in general, can be formed by reacting hydrogen peroxide with the appropriate acyl chloride or anhydride, under such conditions that an intermediate reacts with a second acyl chloride or anhydride molecule.
- 2,2'-dicarboxydicyclohexanoyl peroxide can be formed by reacting particulate cis or trans cyclohexane-1,2-dicarboxylic anhydride with hydrogen peroxide employing substantially the minimum amount of liquid in which to suspend the cyclohexane-1,2-dicarboxylic anhydride, at a pH of about 2 and at a temperature of about 40° C.
- the peroxyacids and peroxides are formed in the presence of diluents described hereinbefore, so that at no stage is pure active oxygen containing product isolated.
- bleaching compositions according to the present invention were compared with conventional inorganic persalts in washing stained fabrics with 1 liter water containing 4 gms of a detergent composition comprising linear alkyl benzene sulphonate 15%, sodium tripolyphosphate 37% sodium silicate 6%, coconut monoethanolamide 3%, sodium carboxy methylcellulose 1.5%, water 6% and balance sodium sulphate, the %s being by weight, and sufficient active oxygen-containing compounds to yield 35 ppm active oxygen in solution.
- the washing was carried out at a temperature in the range of 30 to 60° C. and at a pH of 9.
- the oxygen-containing compounds consisted of (a) sodium perborate tetrahydrate, (included for comparison) (b) 2-peroxycarboxycyclohexanecarboxylic acid and (c) 2-peroxycarboxycyclohex-3-enecarboxylic acid.
- the fabrics comprised cotton or polyester cotton mixtures, and the stains were conventional household stains.
- the stain removal was measured and broadly it was found that (b) and (c) performed substantially the same and better than (a) in the temperature range of 30 to 60° C.
- the washing tests were repeated using the diacyl peroxide analogues of respectively (b) and (c) together with sodium perborate tetrahydrate in a 1:1 mole ratio instead of (b) and (c). Broadly, it was found that the diacyl peroxide/persalt mixtures were also better than sodium perborate in the temperature range of 30 to 60° C. and similar to the peroxyacid themselves.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB52520/75 | 1975-12-23 | ||
GB52520/75A GB1570498A (en) | 1975-12-23 | 1975-12-23 | Peroxides and their use in bleaching compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US4134850A true US4134850A (en) | 1979-01-16 |
Family
ID=10464234
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/683,811 Expired - Lifetime US4134850A (en) | 1975-12-23 | 1976-05-06 | Bleaching composition |
Country Status (8)
Country | Link |
---|---|
US (1) | US4134850A (ja) |
JP (1) | JPS6017786B2 (ja) |
AU (1) | AU2013876A (ja) |
BE (1) | BE849498A (ja) |
DE (1) | DE2657727A1 (ja) |
FR (1) | FR2336393A1 (ja) |
GB (1) | GB1570498A (ja) |
IT (1) | IT1066607B (ja) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4287135A (en) * | 1978-10-25 | 1981-09-01 | Reinhard Stober | Stabilized diperoxyalkanedioic acids and aromatic peroxycarboxylic acids |
US4376218A (en) * | 1980-04-26 | 1983-03-08 | Interox Chemicals Limited | Organic peroxide compositions |
US4385008A (en) * | 1979-10-18 | 1983-05-24 | Interox Chemicals Limited | Bleaching agent |
US4387044A (en) * | 1979-08-13 | 1983-06-07 | Pennwalt Corporation | Safe, dry, free-flowing solid peroxide/unsubstituted or alkyl substituted benzoic acid compositions |
US4391725A (en) * | 1981-10-21 | 1983-07-05 | The Procter & Gamble Company | Controlled release laundry bleach product |
US4482349A (en) * | 1982-01-04 | 1984-11-13 | Monsanto Company | Substituted-butanediperoxoic acids and process for bleaching |
US4487723A (en) * | 1982-01-04 | 1984-12-11 | Monsanto Company | Substituted-butanediperoxoic acids and process for bleaching |
EP0206624A2 (en) | 1985-06-14 | 1986-12-30 | The Procter & Gamble Company | Diperoxy acids and bleaching therewith |
US4756844A (en) * | 1986-12-29 | 1988-07-12 | The Dow Chemical Company | Controlled-release composition having a membrane comprising submicron particles |
US4923753A (en) * | 1987-03-26 | 1990-05-08 | The Dow Chemical Company | Controlled-release compositions for acids |
US5409633A (en) * | 1992-09-16 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Bleach composition |
WO1995019132A1 (en) * | 1994-01-15 | 1995-07-20 | The Procter & Gamble Company | Diacyl and tetraacyl peroxides to inhibit transfer of bleachable food soil in machine dishwashing |
US5707953A (en) * | 1993-04-19 | 1998-01-13 | Akzo Nobel N.V. | Fluidized bed coated amidoperoxyacid bleach composition |
US5985815A (en) * | 1993-11-25 | 1999-11-16 | Warwick International Group Limited | Bleach activators |
US5989530A (en) * | 1992-03-10 | 1999-11-23 | Goldwell Ag | Bleaching composition for human hair and process for its production |
US6007735A (en) * | 1997-04-30 | 1999-12-28 | Ecolab Inc. | Coated bleach tablet and method |
EP0588622B2 (en) † | 1992-09-16 | 2002-12-04 | Unilever Plc | Bleach composition |
US20100092407A1 (en) * | 2007-03-23 | 2010-04-15 | Mitsubishi Gas Chemical Company, Inc. | Tooth-bleaching material and method of bleaching tooth |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0028432B1 (en) * | 1979-11-03 | 1984-01-18 | THE PROCTER & GAMBLE COMPANY | Granular laundry compositions |
JPH01136682A (ja) * | 1987-11-24 | 1989-05-29 | Sanyo Shokai:Kk | パチンコ店等における景品相当カード・シート出券方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2795618A (en) * | 1953-06-26 | 1957-06-11 | Monsanto Chemicals | Organic peroxides |
US3211773A (en) * | 1961-04-26 | 1965-10-12 | Hoechst Ag | Cycloalkyl percarbonate esters |
US3538011A (en) * | 1966-06-23 | 1970-11-03 | Chefaro Maalschappij Nv | Stabilized compositions containing organic peroxides,and methods for the production thereof |
US3574519A (en) * | 1968-10-02 | 1971-04-13 | Atlantic Richfield Co | Method for bleaching textiles |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2335856A (en) * | 1940-11-23 | 1943-12-07 | Lucidol Corp | Organic peroxide composition |
FR1354160A (fr) * | 1963-01-11 | 1964-03-06 | Air Liquide | Procédé de préparation de mélanges oxydants à base d'acide monoperphtalique |
BE693035A (ja) * | 1966-03-03 | 1967-07-03 |
-
1975
- 1975-12-23 GB GB52520/75A patent/GB1570498A/en not_active Expired
-
1976
- 1976-05-06 US US05/683,811 patent/US4134850A/en not_active Expired - Lifetime
- 1976-12-01 AU AU20138/76A patent/AU2013876A/en not_active Expired
- 1976-12-17 BE BE1007832A patent/BE849498A/xx not_active IP Right Cessation
- 1976-12-17 FR FR7638621A patent/FR2336393A1/fr active Granted
- 1976-12-20 IT IT52707/76A patent/IT1066607B/it active
- 1976-12-20 DE DE19762657727 patent/DE2657727A1/de not_active Withdrawn
- 1976-12-23 JP JP51155631A patent/JPS6017786B2/ja not_active Expired
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2795618A (en) * | 1953-06-26 | 1957-06-11 | Monsanto Chemicals | Organic peroxides |
US3211773A (en) * | 1961-04-26 | 1965-10-12 | Hoechst Ag | Cycloalkyl percarbonate esters |
US3538011A (en) * | 1966-06-23 | 1970-11-03 | Chefaro Maalschappij Nv | Stabilized compositions containing organic peroxides,and methods for the production thereof |
US3574519A (en) * | 1968-10-02 | 1971-04-13 | Atlantic Richfield Co | Method for bleaching textiles |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4287135A (en) * | 1978-10-25 | 1981-09-01 | Reinhard Stober | Stabilized diperoxyalkanedioic acids and aromatic peroxycarboxylic acids |
US4387044A (en) * | 1979-08-13 | 1983-06-07 | Pennwalt Corporation | Safe, dry, free-flowing solid peroxide/unsubstituted or alkyl substituted benzoic acid compositions |
US4385008A (en) * | 1979-10-18 | 1983-05-24 | Interox Chemicals Limited | Bleaching agent |
US4403994A (en) * | 1979-10-18 | 1983-09-13 | Interox Chemicals Limited | Bleaching agents |
US4376218A (en) * | 1980-04-26 | 1983-03-08 | Interox Chemicals Limited | Organic peroxide compositions |
US4391725A (en) * | 1981-10-21 | 1983-07-05 | The Procter & Gamble Company | Controlled release laundry bleach product |
US4482349A (en) * | 1982-01-04 | 1984-11-13 | Monsanto Company | Substituted-butanediperoxoic acids and process for bleaching |
US4487723A (en) * | 1982-01-04 | 1984-12-11 | Monsanto Company | Substituted-butanediperoxoic acids and process for bleaching |
EP0206624A2 (en) | 1985-06-14 | 1986-12-30 | The Procter & Gamble Company | Diperoxy acids and bleaching therewith |
US4756844A (en) * | 1986-12-29 | 1988-07-12 | The Dow Chemical Company | Controlled-release composition having a membrane comprising submicron particles |
US4923753A (en) * | 1987-03-26 | 1990-05-08 | The Dow Chemical Company | Controlled-release compositions for acids |
US5989530A (en) * | 1992-03-10 | 1999-11-23 | Goldwell Ag | Bleaching composition for human hair and process for its production |
US5409633A (en) * | 1992-09-16 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Bleach composition |
EP0588622B2 (en) † | 1992-09-16 | 2002-12-04 | Unilever Plc | Bleach composition |
US5707953A (en) * | 1993-04-19 | 1998-01-13 | Akzo Nobel N.V. | Fluidized bed coated amidoperoxyacid bleach composition |
US5985815A (en) * | 1993-11-25 | 1999-11-16 | Warwick International Group Limited | Bleach activators |
WO1995019132A1 (en) * | 1994-01-15 | 1995-07-20 | The Procter & Gamble Company | Diacyl and tetraacyl peroxides to inhibit transfer of bleachable food soil in machine dishwashing |
US6007735A (en) * | 1997-04-30 | 1999-12-28 | Ecolab Inc. | Coated bleach tablet and method |
US20100092407A1 (en) * | 2007-03-23 | 2010-04-15 | Mitsubishi Gas Chemical Company, Inc. | Tooth-bleaching material and method of bleaching tooth |
Also Published As
Publication number | Publication date |
---|---|
GB1570498A (en) | 1980-07-02 |
BE849498A (fr) | 1977-06-17 |
JPS6017786B2 (ja) | 1985-05-07 |
DE2657727A1 (de) | 1977-07-14 |
FR2336393A1 (fr) | 1977-07-22 |
JPS5281081A (en) | 1977-07-07 |
IT1066607B (it) | 1985-03-12 |
AU2013876A (en) | 1978-06-08 |
FR2336393B1 (ja) | 1983-01-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4134850A (en) | Bleaching composition | |
EP0399584B1 (en) | Bleach activation and bleaching compositions | |
US4225451A (en) | Bleaching composition | |
US4128495A (en) | Bleaching composition | |
US4154695A (en) | Bleaching composition | |
EP0484324B1 (en) | Cleaning compositions containing bleach activator compounds | |
EP0331229B1 (en) | Quaternary ammonium compounds for use in bleaching systems | |
EP0392592B1 (en) | Bleach activation | |
US4772412A (en) | Non-aqueous liquid detergent composition comprising perborate anhydrous | |
EP0665876B1 (en) | Granular detergents with protease enzyme and bleach | |
JPH0749597B2 (ja) | 漂白剤触媒及びこれを含有する組成物 | |
CA2176226A1 (en) | Quarternary oxaziridinium salts as bleaching compounds | |
EP0490417A1 (en) | Bleach-builder precursors | |
US5952282A (en) | Sulfonylimine derivatives as bleach catalysts | |
US4927559A (en) | Low perborate to precursor ratio bleach systems | |
DE2614148A1 (de) | Oxidations-, bleich- und waschmittel mit einem gehalt an bleichaktivatoren | |
US5078907A (en) | Unsymmetrical dicarboxylic esters as bleach precursors | |
US5089166A (en) | Bleaching and detergent compositions | |
EP0443640A2 (en) | Bleaching process and use of quaternary ammonium compounds in bleach compositions | |
US5241077A (en) | Peroxyacids | |
WO1995033813A1 (en) | Improved detergent composition | |
EP0333248A2 (en) | Bleach precursors and their use in bleaching and/or detergent composition |